Chief of Staff to the CEO

At Root, we’re on a mission to improve the lives of our customers by offering better insurance solutions. We challenge ourselves to think differently in order to reimagine insurance to make it smarter, more equitable, and a better experience for all.

We strive to “unbreak” the archaic insurance industry by using data and technology in innovative new ways. We believe we must be steadfast in our commitments to research, experimentation, and disciplined data-driven decision making in order to build products our customers love.

The Opportunity

The Chief of Staff (CoS) will maximize the CEO’s effectiveness by managing operational, communication, and strategic initiatives. As a confidante, advisor, and sounding board to the CEO, the CoS will drive clarity, accountability, and alignment across the organization. The CoS builds collaborative relationships with the Executive Leadership Team (ELT) to advance strategic priorities and ensure business results are delivered. This role is operational and strategic with no task being too mundane or too difficult.

Salary Range: $270,000 - $300,000 (Also eligible for competitive bonus and equity offering)

This role requires in-person work in Columbus, Ohio. Candidates must either be located in the Columbus, Ohio area or be open to relocating.

How You Will Make an Impact

Strategic Execution & Prioritization

• Translate strategic initiatives into structured plans, executive briefs, and accountability check-ins. This includes OKRs, departmental initiatives, and board-level deliverables.
• Lead the planning and facilitation of investor updates, executive sessions, press interviews, staff meetings, offsites, and executive retreats. Responsible for agenda development, content curation, day-of logistics, translating outcomes into actionable follow-ups, and tracking their progress.
• Own and maintain the CEO’s to-do list, proactively delegating, advancing tasks, or removing roadblocks. This includes representing the CEO in meetings when necessary.
• Act as an amplifier of the CEO’s priorities and communication, ensuring alignment across teams.
• Partner with the CEO’s executive assistant to anticipate scheduling needs and prepare the CEO with context, talking points, and key documentation.
• Project manage key planning cycles (e.g., annual business planning, executive retreats, quarterly reviews).

Organizational Alignment

• Act as a thought partner and connector between the CEO and senior leadership.
• Anticipate cross-functional blockers and proactively resolve operational misalignments.

Communication & Documentation

• Prepare internal and board-facing communications, briefings, and executive updates.
• Write concise and clear strategic memos, CEO updates, and one-page executive summaries that clarify intent and drive aligned execution.
• Lead the coordination, development, and distribution of materials and briefings for Board of Directors meetings, ensuring all content is comprehensive, polished, aligned with strategic messaging, and delivered in a timely manner.

What You Will Need to Succeed

Experience

• 7+ years in management consulting, strategic operations, business planning, or high-growth startups with at least 5 years of leadership experience.
• Bachelors degree required, MBA preferred.
• Proven success managing fast-paced, multi-stakeholder executive environments.
• Track record of breaking down complex, ambiguous challenges into actionable strategies and driving measurable outcomes.
• Strong financial acumen and comfort interpreting operational KPIs.
• Experience managing or coordinating high-profile deliverables (e.g., board materials, investor decks, CEO communications).
• Familiarity with operating rhythms in founder-led environments and comfort with high-stakes decision-making under pressure.
• Experience navigating business organizations, managing multiple cross-functional stakeholders, and negotiating optimal solutions benefiting all parties.

Skills

• Strong project management, oral and written communication, and organizational skills.
• Ability to drive and implement ideas in an agile environment.
• Structured thinker who can operate at both 30,000 feet and ground level.
• Advanced skills in Notion, Excel/Sheets, presentation software, and project management tools.
• Comfortable using data to drive insights, with a high degree of business acumen and judgment.
• Highly organized and detail-oriented; relentless in follow-through and able to manage multiple workstreams simultaneously.
• Strong ability to push back and influence effectively

As part of Root's interview process, we kindly ask that all candidates be on camera for virtual interviews. This helps us create a more personal and engaging experience for both you and our interviewers. Being on camera is a standard requirement for our process and part of how we assess fit and communication style, so we do require it to move forward with any applicant's candidacy. If you have any concerns, feel free to let us know once you are contacted. We’re happy to talk it through.

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